Although vertical shoot positioned (VSP) training systems, either cane- or spur-pruned, are adopted in the great majority of the vineyards worldwide, the lianas nature of the grapevine and the presence of long and flexible canes confer high plasticity and render structural and pruning changes quite easy. The focus of this review is if, in light of the most consistent features triggered by global warming (e.g., longer growing season, earlier phenology, faster ripening, higher incidence of overheating stress and sunburn, higher frequency of extreme weather events), the type and management of training systems should also be reconsidered. We surveyed the main methods to assess training system efficiency and the current attempts and outlook toward exploiting the training system as an adaptation tool to climate change. For the latter, we considered 12 main trellis types and scored them based on climate-related features and general traits such as vigor, yield control, susceptibility to fungal diseases, and suitability according to wine types (still or sparkling). The resulting balance of positive and negative recommendations leads to a re-evaluation of either old, nonmechanizable trellis types (e.g., Raggi-Bellussi and pergola types), divided canopy systems (e.g., GDC and Scott Henry) or, among the single canopy types, of the single high wire (SHW) trellis. However, historical systems traditionally used by best regions and producers (e.g., goblet and VSP either cane- or spur-pruned) overall show less adherence to the chosen evaluation criteria. To direct future evolution of training systems, regardless of the broadly shared need for suitability to partial or full mechanization, the scenario looks different depending on cool and temperate (warm) areas. The former experiences an outburst of interest as warming is broadening growing areas and affordable genotypes. Under such circumstances, training systems should help accelerate or favor the ripening process through vigor control and lower yield, better cluster exposure, and nonlimiting leaf area-to-fruit ratio. Whereas, in warm areas that are now becoming sub-tropical areas in the worst cases, the SHW gains credit as compared to goblet and traditional VSP. The latter requires an increasing number of canopy manipulations and a rethinking of some planting choices to accommodate the needs of slower and more delayed ripening, more cluster shading, and higher cordons, the latter reducing the probability of incurring significant frost damag